Airbnb Investment Analysis: 102 Anglers Way, Islamorada, FL 33036

Weak · financed

Priced too high to cash-flow with a loan — an equity or tax play, not income.

102 Anglers Way

Islamorada, FL 33036

2bd · 2ba · 6 guests

Purchase price

Est. monthly payment$2,495/mo

Break-even price$403.4K

Vs 2 comps nearby#2 of 3

$29.4K$64.0K

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Investment potential

Your scenario · adjust the levers below or open advanced settings to see how returns change

Projected annual revenue

$46,674

$3,890/mo · at 54% occupancy & $292/night

Cash-flow negative

-$5,782

-$482/mo after costs & mortgage

Cap rate

4.8%

Cash-on-cash

-3.9%

DSCR

0.81

Confidence

43%

Your assumptions

Revenue

$46,674/yr

Market avg: $46,674/yr · 54% occ · $292 ADR

Occupancy

mkt

Avg daily rate

mkt

Days available

Financing

$29,939/yr

Down payment

Interest rate

Mortgage term

Operating costs

$22,518/yr

Property management

Airbnb fee

Property tax

Insurance

Utilities

Market Context

How this property compares to similar short-term rentals nearby.

Comparable set · 2 properties

Daily rate

$273–$311

Median $292

Occupancy

45%–62%

Median 54%

Annual revenue

$29.4K–$64.0K

Median $46.7K

Days available

253–348

Median 301

Revenue floor · $29.4KTop performer · $64.0K

This property · $46.7K

Comparable properties (2)

Cash flow potential Low · Appreciation potential Medium

RevenueOccupancyDaily rate

Casa SeagullsTop performer

348 days available · 216 days booked ·

Annual revenue

$63,979

Occupancy

62%

Daily rate

$311

Beautiful Sunsets

253 days available · 114 days booked ·

Annual revenue

$29,369

Occupancy

45%

Daily rate

$273

Revenue and occupancy reflect Chalet's modeled estimates from observed booking activity for comparable active listings. Individual results vary with management, seasonality, and pricing.

Who this property is for

Three ways this deal works — and who each one fits

The same property is a great buy for one investor and a trap for another. Here's the honest read.

Best fit

1031 / high-equity buyer

~$123.5K

Year-1 tax shield

Buying with cash or low leverage removes the debt-coverage problem entirely, so the thesis rests on appreciation plus a large first-year write-off. At roughly 25% of purchase price, the shield is substantial enough to carry the deal on its own.

Workable

Price-disciplined buyer

$403.4K

Break-even purchase price

The deal pencils only if you buy right. At ~19% below the Zestimate the numbers reach break-even — treat that as a negotiation anchor, not a fantasy. Pay asking and the math stops working.

Not a fit

DSCR cash-flow buyer

0.81

DSCR at asking

At asking price the property doesn't cover its own debt service, so it won't qualify for DSCR financing as modeled. If you need cash flow from day one, look at a mid-term-rental fallback or a different Islamorada submarket.

Year-one tax shield estimate

For a buyer who materially participates and qualifies for the STR tax treatment.

$123.5K

Estimated first-year deduction · range $102.5K–$140.8K

Purchase price: $500,000
Land allocation (excluded): −$175,000
Depreciable basis: $325,000
Cost-seg accelerated: $97,500
+ Bonus depreciation & furnishings: $26,000

Why this matters here

At a marginal bracket, this deduction can be worth $37.9K–$52.1K in estimated federal tax saved.

This only applies if you meet the IRS material-participation tests for short-term rentals and are not using a full-service property manager.

Estimate, subject to CPA review. Cost-segregation percentages shown here are illustrative and depend on an actual study of the property.

Some states do not conform to federal bonus depreciation, so your state may not allow the same first-year treatment shown above.

Chalet can introduce a cost-segregation partner — this is not tax, legal, or financial advice.

Price sensitivity & break-even

How cash-on-cash return moves with purchase price. The marked line is break-even (1.0 DSCR).

Purchase price$500,000 (+0.0% vs asking)

At this price: cash-on-cash -3.9%, DSCR 0.81, cash flow -$5,782/yr

Cash-on-cash return by purchase price
Price vs asking	Price	Cash-on-cash	DSCR	Band
-25%	$375,000	1.4%	1.08	Positive
-22%	$390,000	0.7%	1.03	Positive
-15%	$425,000	-1.0%	0.95	Below break-even
-8%	$460,000	-2.4%	0.88	Below break-even
Asking	$500,000	-3.9%	0.81	Below break-even
+8%	$540,000	-5.1%	0.75	Below break-even
+15%	$575,000	-6.1%	0.70	Below break-even

Below break-evenAt break-evenPositive

Break-even price

$403,432

~19% under Zestimate. Where this property reaches 1.0 DSCR and neutral cash flow.

Discount needed

−$96,568

The gap between asking and the price a cash-flow buyer can underwrite.

If refi to 5.5% in 24 mo

+$4,388/yr

Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.

Gross revenue$46,674

Booking & management fees−$6,068

Airbnb fee (3%)$1,400

Property mgmt (10%)$4,667

Net revenue

$40,606

Property operating costs−$16,450

Insurance, utilities & maintenance$11,450

Property tax (est.)$5,000

Net operating income (NOI)Before mortgage · 52% margin

$24,156

Debt service (mortgage)−$29,939

Annual cash flow−$5,782

−$482/mo after all expenses

Cash to close

Down payment, closing costs, and furnishing

$145,000

Return on cash:13.3%

Down payment

25% of purchase price

$125,000

Closing costs

1% of purchase price

$5,000

Furnishing budget

2BR · est. 3% of purchase price

$15,000

DSCR below 1.0 — but you can still qualify

Your DSCR is 0.81 · lenders typically require 1.0+.

01.0 threshold2.0+

Get matched with 2–3 vetted STR lenders, free.

Return & exit scenario

What the deal returns over the hold — including the tax shield, which is the whole point for an appreciation buyer.

Levered IRR

15.4%

over 5-yr hold, with tax shield

Equity multiple

1.9×

total proceeds vs. $145,000 invested

Projected value at exit

$638,141

year 5 · 5.0% annual appreciation

Tax shield contribution

+6.7 pts

of IRR comes from year-1 depreciation

Equity builtAppreciationCumulative cash flow (netted into total)

Projected investment value by year
Year	Equity	Appreciation	Cumulative cash flow	Total value
Year 1	$128,809	$25,000	$39,913	$193,722
Year 2	$132,894	$51,250	$34,831	$218,975
Year 3	$137,274	$78,813	$30,460	$246,546
Year 4	$141,970	$107,753	$26,810	$276,533
Year 5	$147,007	$138,141	$23,892	$309,039

Projection, not a promise.

Assumes 5.0% annual appreciation, 1.5% rent growth (operating costs held flat), and that the property qualifies for short-term-rental tax treatment. The year-1 depreciation shield depends on a real cost-segregation study and your tax situation — consult a CPA.

Appreciation is the dominant driver of this return. When cash flow is negative, the deal depends on the property gaining value — it is not paying for itself from income.

Appreciation, rent growth, and financing rates are editable under Edit financials.

Get a Islamorada STR agent who understands this deal.

STR deals turn on local rules and demand that a generalist agent misses. Chalet matches you with a vetted Islamorada agent who knows which properties actually cash flow — and which to avoid.

Vetted STR specialistsFree to investorsNo obligation

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Disclaimer. This page and the data presented are for informational purposes only. The information provided should not be construed as financial, legal, or investment advice. Market conditions can change rapidly, and past performance does not guarantee future results. Always consult with qualified professionals before making investment decisions.

TOOLS & CALCULATORS

LEARNING & RESOURCES

SERVICES & PARTNERS

MARKET INSIGHTS

Three ways this deal works — and who each one fits

Year-one tax shield estimate

Price sensitivity & break-even

Return & exit scenario

Get a Islamorada STR agent who understands this deal.

Popular Airbnb Investment Opportunities Near This Property (Analyzed by Chalet Users)

Popular Airbnb Investment Opportunities Near This Property (Analyzed by Chalet Users)